title: Isothiourea-mediated one-pot synthesis of functionalized pyridines.
abstract: Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N- to O-sulfonyl migration, giving 2-sulfonate-substituted pyridines which are readily derivatized to generate structural diversity.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST (UK) http://ch-www.st-andrews.ac.uk/staff/ads/group/
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Stark
authors.forename: Louis C
authors.initials: LC
authors.lastname: Morrill
authors.forename: Pei-Pei
authors.initials: PP
authors.lastname: Yeh
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Timothy J C
authors.initials: TJ
authors.lastname: O'Riordan
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D011725:Pyridines; D013890:Thiourea
keywords: Lewis base; cyclization; heterocycles; isothiourea; organocatalysis